2-Methylbenzaldehyde → HCID 19769730, compound

HRID 1590169Notes

Reaction equation

HRID 1590169 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O.[C:16]([O:25]CC)(=[O:24])[CH2:17][CH2:18][C:19]([O:21]CC)=[O:20]>C(O)(C)(C)C>[CH3:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1/[CH:10]=[C:18](\[CH2:17][C:16]([OH:25])=[O:24])/[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 107222-MethylbenzaldehydeHCID 31249Diethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19769730HCID 19769730, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of potassium t-butoxide (8.5 g) in t-butanol (100 ml) was added a mixture of 2-methylbenzaldehyde (6.0 g) and diethyl succinate (12.0 g) and the mixture was refluxed for 3 hours. After the solvent was evaporated under reduced pressure, 10% sodium hydroxide solution (100 ml) was added to the resulting residue and the mixture was refluxed for 5 hours. The reaction mixture was acidified with hydrochloric acid under ice-cooling and the precipitated crystals were collected by filtration to give 3.6 g of (E)-2-methylbenzylidenesuccinic acid.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customAfter the solvent was evaporated under reduced pressure, 10% sodium hydroxide solution (100 ml)
  3. additionwas added to the resulting residue
  4. temperaturethe mixture was refluxed for 5 hours
  5. temperaturecooling
  6. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-cd65c638da87463e8076075ac72408f0
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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